WO2011114010A1

WO2011114010A1 - Cosmetic use of an imidoperoxycarboxylic acid derivative for reducing skin pore size

Info

Publication number: WO2011114010A1
Application number: PCT/FR2010/052787
Authority: WO
Inventors: Francine Baldo
Original assignee: L'oreal
Priority date: 2010-03-17
Filing date: 2010-12-17
Publication date: 2011-09-22
Also published as: FR2957522B1; FR2957522A1

Abstract

The invention relates to the cosmetic use of an imidoperoxycarboxylic acid compound having the following formula (I): in which: - A is an optionally substituted benzene ring - R is hydrogen atom, an -OH group, a (C₁-C₅)alkyl group, a -COOH group or a -COOR₁ group, R₁ being a (C₁-C₅)alkyl group, and - n is an integer ranging from 1 to 5, and salts thereof, in a cosmetic composition comprising a physiologically acceptable aqueous medium, as an agent intended for reducing the appearance and/or the visibility of pores. The invention also relates to a cosmetic method intended for reducing the appearance and/or the visibility of skin pores, comprising the topical application to the skin of a composition comprising an imidoperoxycarboxylic acid compound.

Description

Cosmetic use of an imido-peroxycarboxylic acid derivative to reduce the pore size of the skin

The invention relates to the cosmetic use of at least one imidoperoxycarboxylic acid derivative, in a composition comprising a physiologically acceptable medium, as an agent intended to reduce the appearance and / or the visibility of the pores, in particular at the level of facial skin.

Men and women, regardless of their age, are concerned with the appearance of their skin, especially in their face. The skin of the face can be marked by the presence of wrinkles and fine lines, stains, hyperpigmentations, dark circles, puffiness, loss of elasticity, but also by the presence of dilated and visible pores.

The appearance and / or visibility of pores is a problem that is sought to be addressed, particularly in people with dilated pores regardless of their origin: ethnic (eg Asian population, Caucasian populations), excess of sebum, aging, loss of firmness, relaxation, stress, fatigue, inadequate hygiene, climatic factors ....

This imperfection of the skin, especially in the face and in particular the T-zone (forehead, nose, cheeks, chin), in particular of the area of the nose and cheeks, may be accentuated by an increase in the width of the skin. conical portion around the pore and / or a state of parakeratosis of the stratum corneum at this conical portion, itself sometimes linked to excessive secretion of sebum and unsaturated fatty acids. It is known from the prior art the use of makeup compositions, which may contain silicas or polymers, as described in US2006257346 or WO05048958 application, to camouflage this skin imperfection.

It is also known, in order to reduce the pore size and thus improve the appearance of the skin, the use of astringent lotions which may contain astringent salts of the AI salt type, or hydroalcoholic solutions (WO 2006/056246), or combinations of retinoids and hydroxycarboxylic acids (AHA), or parakeratosis inhibitors such as glycine derivatives (WO05051340), or hair growth inhibitors (WO05120451). But there remains the need for non-irritating active ingredients and particularly well tolerated by the skin, having an effectiveness on the appearance and / or visibility of the pores, in particular the tightening, so on the reduction of the size of the expanded pores , thus making them less visible. Reducing the size of the pores also reduces the brightness of the skin.

However, the Applicant has just demonstrated by a clinical study that the use of imido-peroxycarboxylic acid derivatives, in particular of 6-phthalimidoperoxyhexanoic acid, makes it possible to reduce the visibility of the pores of the skin and / or reduce the shine of the skin.

6-Phthalimidoperoxyhexanoic acid is a compound marketed by SOLVAY as a deodorant, bacteriostatic and decolorizing active agent.

US Pat. No. 6,471,947 discloses a cosmetic oral cosmetic composition for bleaching teeth containing 6-phthalimidoperoxyhexanoic acid.

WO 2005/068470 discloses aqueous compositions comprising 6-phthalimidoperoxyhexanoic acid and a nonionic surfactant.

Cosmetic compositions comprising 6-phthalimidoperoxyhexanoic acid are also described in EP-A-2105165 and WO 2009/001296.

The invention therefore relates to the cosmetic use of at least one imidoperoxycarboxylic acid derivative as defined hereinafter, in a cosmetic composition comprising a physiologically acceptable aqueous medium, as an agent intended to reduce the appearance and / or the visibility of the pores.

In particular, the imido-peroxycarboxylic acid derivative is intended to tighten the pores and / or reduce the pore size, and / or reduce the number of visible pores.

The invention also relates to a cosmetic method for reducing the appearance and / or the visibility of the pores of the skin, comprising the topical application to the skin, in particular on a skin having visible pores, of a composition comprising at least one minus an imido-peroxycarboxylic acid derivative as defined below.

This process is intended in particular to reduce the visibility of the pores of oily skin, aged skin, especially photoaggloss, or ethnic skin, in particular Asian skin and Caucasian skin. The imido-peroxycarboxylic acid derivative used in the composition according to the invention is chosen from the compounds of formula (I) below:

in which :

A represents a benzene ring optionally substituted with one or more, preferably up to 4, and even more preferably with 1 or 2 groups chosen from a (C ₁ -C ₅ ) alkyl group,

R, identical or different, represents a hydrogen atom, an -OH group, a (C ₁ -C ₅ ) alkyl group, a -COOH group, a -COOR 1 group, R 1 representing a (C ₁ -C ₅ ) alkyl group, and

n is an integer ranging from 1 to 5, for example from 1 to 3 or for example from 3 to 5, and their salts.

The salts of the compounds that may be used according to the invention are in particular chosen from alkali metal salts, for example sodium and potassium; alkaline earth metal salts, for example calcium, magnesium, strontium, metal salts, for example zinc, aluminum, manganese, copper; ammonium salts of formula NH ₄ ⁺ ; quaternary ammonium salts; organic amine salts, such as for example the salts of methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2-hydroxyethylamine, bis- (2-hydroxyethyl) amine, tri- (2- hydroxyethyl) amine; lysine salts, arginine. Salts chosen from among the sodium, potassium, magnesium, strontium, copper, manganese and zinc salts are preferably used. Preferably, the sodium salt is used.

Examples of (C ₁ -C ₅ ) alkyl groups are methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, and pentyl.

According to one embodiment, an imido-aromatic percarboxylic acid derivative of formula (I) is used, for which A is an unsubstituted benzene ring, R is a hydrogen atom, a -COOH group or a (CrC _{3) group.} ), and n ranges from 3 to 5. Preferably, R is a hydrogen atom.

Preferably, A represents an unsubstituted benzene ring.

Among the compounds of formula (I), mention may be made of phthalimido-peroxyacetic acid (A = benzene, R = H, n = 1), 2-phthalimido-peroxy-propionic acid, 3-phthalimido-peroxypropionic acid (A = benzene, R = H; n = 2), 4-phthalimidoperoxybutanoic acid, 3-phthalimidoperoxybutanoic acid, phthalimidoperoxypentanoic acid, phthalimidoperoxyhexanoic acid, phthalimidoperoxyhexanoic acid, phthalimidoperoxyheptanoic acid, phthalimidoperoxyoctanoic acid, phthalimidoperoxynonanoic acid, phthalimidoperoxydecanoic acid, phthalimidoperoxyundecanoic acid, phthalimidoperoxydodecanoic acid, 2-phthalimido-mono-peroxysuccinic acid.

Preferably, the compound of formula (I) is phthalimidoperoxyhexanoic acid, also called phthalimidoperoxycaproic acid, ε-phthalimidoperoxyhexanoic acid. Its chemical structure is as follows:

It corresponds to a compound of formula (I) in which R represents a hydrogen atom, A represents an unsubstituted benzene ring and n = 5. It is called I phthalimidoperoxycaproic acid.

6-Phthalimidoperoxyhexanoic acid (abbreviated as PAP) is in particular available in two commercial forms by SOLVAY. The 6-phthalimidopéroxyhexanoïque acid is also available as an aqueous dispersion (17% active material) under the trade name EURECO ^® HC L17 by the company Solvay.

The 6-phthalimidopéroxyhexanoïque acid is also provided in the form of a powder under the tradename EURECO ^® HC-P1 1.

Aqueous dispersions of 6-phthalimidoperoxyhexanoic acid are described in EP 1 074 607. These aqueous dispersions are stabilized by copolymers of methyl vinyl ether with maleic acid and / or maleic anhydride in a 1: 1 ratio. having an alternating structure.

The amount of PAP to be used in a composition according to the invention depends on the desired cosmetic effect, and can therefore vary to a large extent.

Those skilled in the art can easily, on the basis of their general knowledge, determine the appropriate quantities. The imido-peroxycarboxylic acid derivative of formula (I) may be present in the composition used according to the invention in a content ranging from 0.0001% to 30% by weight, relative to the total weight of the composition. Preferably, the content of said compound of formula (I) can range from 0.001% to 20% by weight, relative to the total weight of the composition. In particular, the content of said compound of formula (I) can range from 0.01% to 20% by weight, relative to the total weight of the composition.

Preferably, the content of said compound of formula (I) may range from 0.05% to 5% by weight, relative to the total weight of the composition. Advantageously, the composition used according to the invention may comprise a copolymer of 2-acrylamido-2-methylpropanesulfonic acid and hydroxylated (C 2 -C 4) alkyl (meth) acrylate, optionally salified.

The C2-C4 alkyl (meth) acrylate hydroxyl monomer may be chosen from 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2,3-dihydroxypropyl acrylate, 2,3-methacrylate and 2,3-dihydroxypropyl acrylate. -dihydroxypropyle.

Said copolymer may be salified, in particular in the form of an alkali metal salt such as, for example, the sodium or potassium salt, or in the form of an ammonium salt, or in the form of a salt of an aminoalcohol such as, for example, salt monoethanolamine, or in the form of an amino acid salt such as, for example, the lysine salt.

Advantageously, the copolymer is salified in the form of sodium salt.

Preferably, the composition comprises the copolymer of 2-acrylamido-2- methylpropane sulfonic acid and acrylate, 2-hydroxyethyl, in particular as sodium salt, such as those sold under the trade names "Sepinov ^® EMT 10 "or" SIMULGEL ^® NS "by the company SEPPIC (INCI name: Hydroxyethyl acrylate / sodium acryloyldimethyl taurate copolymer). Such polymers are described in application FR-A-2856691.

The copolymer of 2-acrylamido-2-methylpropanesulfonic acid and of C2-C4 alkyl (meth) acrylate hydroxylated may be present in the composition according to the invention in a content ranging from 0.05% to 20% by weight, relative to the total weight of the composition. Preferably, the content of said copolymer may range from 0.1% to 10% by weight, relative to the total weight of the composition. Preferably, the content of said copolymer can range from 0.5% to 5% by weight, relative to the total weight of the composition.

Advantageously, the imido-peroxycarboxylic acid derivative of formula (I) (referred to as A) and the copolymer of 2-acrylamido-2-methylpropanesulfonic acid and of C2-C4 alkyl (meth) acrylate hydroxylated (said B) may be present in the composition used according to the invention in a weight ratio A / B ranging from 1/5 to 5/1. Preferably, this A / B weight ratio can range from 1/3 to 3/1. Preferably, this weight ratio A / B may range from 0.4 to 1.1. More preferably, this weight ratio A / B can range from 0.5 to 1.

The composition used according to the invention comprises a physiologically acceptable aqueous medium, ie a non-toxic aqueous medium that can be applied to human keratin materials and has a pleasant appearance, odor and feel. . The composition is in particular a cosmetic composition.

The composition used according to the invention comprises water, for example in a content ranging from 50% to 99% by weight, relative to the total weight of the composition. Preferably, the water content in the composition may range from 60% to 97% by weight.

Advantageously, the composition used according to the invention has a pH ranging from 3 to 5. Preferably, the pH of the composition ranges from 3.5 to 4.2.

The pH of the composition may be adjusted, for example, with sodium hydroxide, citric acid of sodium citrate, potassium citrate, lactic acid, sodium lactate, potassium lactate or glycolic acid. , sodium glycolate, potassium glycolate.

According to one embodiment of the invention, the composition may comprise at least one oil chosen from linear or branched C 5 -C 15 alkanes, linear or cyclic polydimethylsiloxane silicone oils having from 2 to 7 silicon atoms, such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, hexamethyl disiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, polydimethylsiloxanes (and preferably those having a viscosity of less than 200), triglycerides of capric / caprylic acids (such as those sold under the name MIGLYOL 812 N by the company SASOL or MYRITOL 318 by the company COGNIS). The oil may be present in the composition used according to the invention in a content ranging from 0.05% to 50% by weight, relative to the total weight of the composition. Preferably, said oil may be present in a content ranging from 0.1% to 30% by weight, relative to the total weight of the composition. Preferably, said oil may be present in a content ranging from 1% to 20% by weight, relative to the total weight of the composition.

The composition used according to the invention may further contain a stable cosmetic active at acidic pH. It may contain an asset chosen from:

ascorbic acid, kojic acid, caffeic acid, salicylic acid and its derivatives, citric acid, lactic acid, methyllactic acid, glucuronic acid, glycolic acid, pyruvic acid, 2-hydroxy-butanoic acid, 2-hydroxypentanoic acid, 2-hydroxyhexanoic acid, 2-hydroxyheptanoic acid, 2-hydroxyoctanoic acid, 2-hydroxy-nonanoic acid, 2-hydroxydecanoic acid, 2-hydroxyundecanoic acid, 2-hydroxydodecanoic acid, 2-hydroxy-tetradecanoic acid, 2-hydroxy-hexadecanoic acid, 2-hydroxy-octadecanoic acid, acid 2-hydroxytetra-cosanoic acid, 2-hydroxy-eicosanoic acid, mandelic acid, benzoic acid, phenyllactic acid, gluconic acid, galacturonic acid, aleuritic acid, ribonic acid, tartaric acid, tartaric acid, malic acid, fumaric acid, retinoic acid and its derivatives, benzene-1,4-di (3-methylidene 10-camphosulfoic acid) urocanic acid, 2-phenyl benzimidazole 5-sulphonic acid, α- (2-oxo-2-bornylidene) toluene-4-sulfonic acid, 2-hydroxy-4-methoxy-5-acid sulfonic acid, plant extracts containing acids and more particularly fruit extracts, acidic xanthic derivatives, β-glycyrrhetinic acid, Asian acid and mixtures thereof.

The composition may also comprise other cosmetic additives, provided that the stability of the compound of formula (I) is maintained. As cosmetic additives can for example be made of xanthan gum, the copolymer polyvinyl methyl ether / maleic acid (such as that sold under the name Gantrez ^® S-97 BF by ISP),

The composition used according to the invention may be in the form of an aqueous gel or an oil-in-water (O / W) emulsion.

The invention will now be illustrated by the following nonlimiting examples: EXAMPLE 1 Demonstration of the Effect of 6-Phthalimidoperoxyhexanoic Acid on the Pore Tightening The following composition was prepared:

- 6-phthalimidoperoxyhexanoic acid in aqueous dispersion

at 17% MA (EURECO HC L17® from Solvay) 0.85% MA ie 5% as is

sodium acrylamido 2-methyl propane sulfonate copolymer

90% 2-hydroxyethyl methacrylate in water

(SEPINOV EMT 10 from Seppic) 1, 8% MA or 2% as is

- 0.012% sodium hydroxide

- water qs 100%

A randomized, double-blind clinical study was performed on a group of 40 women aged 14 to 40 years with oily and mixed-oily skin.

The composition was applied to the finger on the face, one application 2 times a day (morning and evening), for 8 weeks. The pore size was measured before and after treatment of the skin using the Dermascore® device according to the protocol described in the article: Quantification of facial pores using image analysis Ghislain François et al, Cosmetic dermatology, vol 22, n 9, pages 457-463.

The Dermascore is a tool that allows the visualization of skin pores using a lens to magnify objects (x3) and using the polarization properties of light incident to the object (to see the pores a parallel polarization of the light is used).

A clinical scoring of the pore size was performed at To, T5days, T 4 weeks, T8 weeks on each person in the pannels.

The scoring of the pore size was done with an atlas as described in the aforementioned artcile. The atlas assigns a grade 0 to 5 according to the appearance of the pore visualized

(keep 0 = little or no visible pores, grade 5 = large, very visible pores).

The set of measurement data was compiled and a statistical analysis was performed (2-way analysis of variance (time x woman) followed by a Dunnett test comparing all times to T0.The analysis was performed on rows if the normality assumption was rejected by Shapiro Wilk's test at 1%). The variation over time (5 days, 4 weeks, 8 weeks) was then determined with respect to T0 of the pore size evaluation (according to atlas grades).

The following results were obtained:

The results obtained showed that the composition containing 6-phthalimidoperoxyhexanoic acid makes it possible to obtain a significant reduction in the pore size of the facial skin as of the fifth day of treatment and this reduction in pore size is also observed after 8 weeks of treatment.

Claims

1. Cosmetic use of at least one imido-peroxycarboxylic acid compound of formula (I) below:

in which :

R, identical or different, represents a hydrogen atom, an -OH group, a (C ₁ -C ₅ ) alkyl group, a -COOH group, a -COOR ₁ group, R ₁ representing a (C ₁ -C ₅ ) alkyl group, and

n is an integer ranging from 1 to 5, for example from 1 to 3 or for example from 3 to 5, and their salts;

in a cosmetic composition comprising a physiologically acceptable aqueous medium, as an agent intended to reduce the appearance and / or the visibility of the pores.

2. Use according to claim 1, characterized in that the compound of formula (I) is intended to tighten the pores and / or reduce the pore size, and / or reduce the number of visible pores.

3. Use according to one of the preceding claims, characterized in that for the compound of formula (I) A is an unsubstituted benzene ring, R is a hydrogen atom, a -COOH group or a group (CrC ₃ ), and n varies from 3 to 5.

4. Use according to any one of the preceding claims, characterized in that the compound of formula (I) is 6-phthalimidoperoxyhexanoic acid.

5. Use according to any one of the preceding claims, characterized in that the compound of formula (I) is present in a content ranging from 0.0001% to 30% by weight, relative to the total weight of the composition, preferably ranging from 0.001% to 20% by weight, preferably ranging from 0.01% to 20% by weight, and more preferably ranging from 0.05% to 5% by weight.

6. Use according to any one of the preceding claims, characterized in that the composition comprises a copolymer of 2-acrylamido-2-methylpropanesulfonic acid and C2-C4 alkyl (meth) acrylate hydroxylated.

7. Use according to any one of the preceding claims, characterized in that it also reduces the gloss of the skin.

8. Cosmetic skin treatment process intended to reduce the appearance and / or the visibility of the pores, comprising the application to the skin of the face of a cosmetic composition comprising, in a physiologically acceptable aqueous medium, a compound of imido-peroxycarboxylic acid of formula (I) below:

in which :

9. Process according to the preceding claim, characterized in that for the compound of formula (I) A is an unsubstituted benzene ring, R is a hydrogen atom, a -COOH group or a (CrC ₃ ) alkyl group, and n varies from 3 to 5.

10. Process according to any one of claims 8 or 9, characterized in that the compound of formula (I) is 6-phthalimidoperoxyhexanoic acid.

1. Method according to any one of claims 8 to 10, characterized in that the compound of formula (I) is present in the composition in a content ranging from 0.0001% to 30% by weight, relative to total weight of the composition, preferably from 0.001% to 20% by weight, preferably ranging from 0.01% to 20% by weight, and more preferably ranging from 0.05% to 5% by weight.

12. Process according to any one of Claims 8 to 11, characterized in that the composition comprises a copolymer of 2-acrylamido-2-methylpropanesulfonic acid and of (C 2 -C 4) alkyl (meth) acrylate. hydroxylated, optionally salified.

13. Method according to the preceding claim, characterized in that the monomer of C2-C4 alkyl (meth) acrylate hydroxylated is selected from 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, the acrylate of 2,3-dihydroxypropyl, 2,3-dihydroxypropyl methacrylate.

14. A method according to any one of claims 8 to 13, characterized in that the composition comprises a copolymer of 2-acrylamido-2-methylpropanesulfonic acid and 2-hydroxyethyl acrylate, optionally salified.

15. Method according to any one of claims 8 to 13, characterized in that it is also intended to reduce the brightness of the skin.